Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 645-36-3, name is 2,2-Diethoxyethanamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 645-36-3, Application In Synthesis of 2,2-Diethoxyethanamine

A solution of 1-NAPHTHALENYLTHIOISOCYANATE (893 mg, 4.82 MMOL) and 2- AMINOACETALDEHYDE DIETHYL ACETAL (0.70 mL, 4.85 MMOL) IN TOLUENE (10 mL) was stirred at room temperature for 1 h. Aqueous 12 N HCI solution (0.2 mL) was added and the mixture was heated at 110 C for 3 h and then stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure. The residue was triturated with hot EtOAc to give the title compound (608 mg, 56% yield).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,2-Diethoxyethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2004/50643; (2004); A2;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 592-55-2, name is 1-Bromo-2-ethoxyethane, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2-ethoxyethane

0.24 g (10 mmol) of sodium hydride and 15 ml of N, N-dimethylformamide were added to a 50 ml round bottom flask at room temperatureStir for 10 minutes then add 2.5 g (10 mmol) of compound 2 and 10 mmol2-bromoethylether and trace detection by TLC to the end of the reaction. The reaction mixture was then poured into 500 ml of ice water and extracted three times with 100 ml of ethyl acetate. The organic phases were combined and the solvent was evaporated to dryness. The resulting residue was subjected to silica gel column chromatography Purification (V dichloromethane: V methanol = 100: 1) gave compound 3 (2.4 g, 76% yield).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Guangxi Normal University; Chen Zhenfeng; Liang Hong; Liu Yancheng; Lu Xing; Li Liangping; (13 pag.)CN106632414; (2017); A;,
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Electric Literature of 145903-31-7,Some common heterocyclic compound, 145903-31-7, name is 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine, molecular formula is C10H13NOS, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Synthesis of S19 (Scheme 6): To a stirred solution of S26 (20 mg, 0.1 mmol) and triethylamine (30 mg, 0.3 mmol) in CH2Cl2 (5 ml) is added 1,4-butyldiacid chloride (8 mg, 0.05 mmol) at 0 C. The resulting mixture is stirred at 0 C. for one hour and at room temperature overnight. The organic phase is washed with saturated sodium bicarbonate and 1N HCl and water. After removal of solvent, product S19 is purified by column chromatography (oil, 19 mg, 80% yield). Similarly S22 is prepared from 2,6 pyridyl dicarboxylic acid dichloride.

The synthetic route of 145903-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; US2007/49572; (2007); A1;,
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These common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 2,2-Diethoxyethanamine

(1-1) Synthesis of Compound 1 1-naphthaldehyde (Wako Pure Chemical Industries, Ltd.)(1.56 g, 10 mmol) and 2,2-diethoxyethanamine (TOKYO CHEMICAL INDUSTRY CO., LTD.)(1.33 g, 10 mmol) were mixed and stirred at 100C for 20 min. After the mixture was cooled to room temperature, EtOH (20 mL) was used for dilution. NaBH4 (0.38 g, 10 mmol) was added dropwise and the mixture was stirred at room temperature for 16 h. After completion of the reaction, EtOH was distilled away under reduced pressure. Then, a product was extracted with AcOEt. The resulting product was purified by silica gel column chromatography (hexane/AcOEt = 5/1) to yield compound 1 (2.29 g, 8.5 mmol, 85%).

The synthetic route of 2,2-Diethoxyethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National University Corporation Tottori University; Tokyo Women’s Medical University; SHIOTA, Goshi; HOSHIKAWA, Yoshiko; MATSUMOTO, Noriko; MATSUMI, Yoshiaki; MORIMOTO, Minoru; TONOI, Takayuki; SAIMOTO, Hiroyuki; OHASHI, Kazuo; OKANO, Teruo; EP2698365; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 458-52-6, name is 2-Fluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 458-52-6, category: ethers-buliding-blocks

Step C 2-Fluoro-4-methoxyphenyl isocyanate To a solution of 13.75 g (0.0967 mole) of 2-fluoro-4-methoxyaniline in 120 mL of toluene was slowly added over a period of 30 minutes a solution of 19.13 g (0.0967 mole) of trichloromethyl chloroformate in 30 mL of toluene. During the addition the temperature rose to 35° C. The reaction mixture was stirred without external heating for 30 minutes and then heated at reflux for approximately 17 hours. At the end of this time all of the solvent was removed by distillation, leaving 2-fluoro-4-methoxyphenyl isocyanate as a purple liquid, which was used immediately in Step D.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Fluoro-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FMC Corporation; US5262390; (1993); A;,
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Electric Literature of 150-78-7,Some common heterocyclic compound, 150-78-7, name is 1,4-Dimethoxybenzene, molecular formula is C8H10O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Silfen was freshly prepared by thoroughly grindingFe(NO3)3(H2O)9 (2.0 g) and silica gel (4.0 g; 230-400 mesh) in a mortar [2]. A 25 mLround-bottomed flask was charged with 600 mg of silfen, iodine (142 mg; 1.1 mmol),1,4-dimethoxybenzene (138 mg; 1.0 mmol) and CH2Cl2 (2 mL), and the mixture wasstirred at 25 C overnight. The product was isolated by partitioning the reaction mixturebetween ethyl acetate and water, followed by washing the organic layer with 5% aqsodium thiosulfate and water, and drying (Na2SO4). Concentration by rotary evaporationgave an oil which was purified by CombiFlash chromatography (silica gel; 0-30%CH2Cl2 in hexane over 20 min) to afford a colourless oil (161 mg; 61%). 1H-NMR(CDCl3, 500 MHz): 3.74 (s, 3H, OCH3), 3.81 (s, 3H, OCH3), 6.74 (d, 1H, J = 8.8 Hz, H-6), 6.85 (dd, 1H , J = 8.8, 3.1 Hz, H-5), 7.30 (d, 1H, J = 3.1 Hz, H-3). 13C-NMR (CDCl3,125 MHz): 56.0, 57.1, 86.2, 111.7, 114.7, 125.0, 152.7, 154.3.

The synthetic route of 150-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kempton, Robert J.; Kidd-Kautz, Taylor A.; Laurenceau, Soizic; Paula, Stefan; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 971 – 975;,
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These common heterocyclic compound, 50742-37-5, name is (3-Phenoxyphenyl)methanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of (3-Phenoxyphenyl)methanamine

To a solution of 3-phenoxybenzylamine described in Preparation Example 4 (33mg, 0.167mmol) and benzothiazole-6-carboxylic acid (30mg, 0.167mmol) in tetrahydrofuran (1 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (89mg, 0.20mmol) and triethylamine (28mul, 0.20mmol), and the solution was stirred at room temperature for 17 hours. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane : ethyl acetate), and the title compound (37mg, 62%) was obtained as a colorless oil. 1H-NMR Spectrum (CDCl3) delta(ppm) : 4.68(2H, d, J=6.0Hz), 6.50(1H, brs), 6.94(1H, dd, J=2.0, 8.0Hz), 7.02-7.04(3H, m), 7.11-7.15(2H, m), 7.31-7.37(3H, m), 7.88(1H, dd, J=1.6, 8.8Hz), 8.18(1H, d, J=8.8Hz), 8.49(1H, d, J=1.6Hz), 9.13(1H, s).

The synthetic route of (3-Phenoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
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Reference of 33170-72-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 33170-72-8 as follows.

2-Bromo-1,1-dimethoxypropane (2a) (18 g, 98.34 mmol) was dissolved in chloroform (100 mL), trifluoroacetic acid (67.28 g, 590.03 mmol) was added and reacted at room temperature for 4 hours. The reaction solution was added with dichloromethane (30 mL) and water (15 mL), and the layers were extracted.The organic phase was washed with saturated brine (100 mL x 4), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure at 30 C to give the title compound 2b as a yellow liquid (5 g, 37% yield).

According to the analysis of related databases, 33170-72-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Wei Yonggang; Qiu Guanpeng; Lei Bolin; Li Yao; Wang Song; Zhu Guozhi; (39 pag.)CN106279128; (2017); A;,
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7664-66-6, name is 4-Isopropoxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C9H13NO

To a solution of 4-isopropoxyaniline (9.06 g, 60.0 mmol) in CH2Cl2 (120 mL) and pyridine (30 mL) was added 4-nitrophenyl chloroformate (10.9 g, 54.0 mmol) portionwise with stirring over ~1 min with brief ice-bath cooling. After stirring at room temperature for 1 h, the homogeneous solution was diluted with CH2Cl2 (300 mL) and washed with 0.6 M HCl (1*750 mL) and 0.025 M HCl (1*1 L). The organic layer was dried (Na2SO4) and concentrated to give the title compound as a light violet-white solid (16.64 g, 98%). 1H NMR (CDCl3) delta 8.31-8.25 (m, 2H), 7.42-7.32 (m, 4H), 7.25-7.20 (m, 2H), 6.93 (br s, 1H), 2.90 (sep, J=6.9 Hz, 1H), 1.24 (d, J=6.9 Hz, 6H). LC/MS (ESI) calcd for C16H17N2O5 (MH)+ 317.1, found 633.2 (2 MH)+.

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; US2006/281700; (2006); A1;,
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These common heterocyclic compound, 10541-78-3, name is 2-Methoxy-N-methylaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C8H11NO

To a stirring dichloromethane (40 mL) solution containing 5-bromo-4- chloro-2-hydroxybenzoic acid (2.0 g, 8.0 mmol), were added triethylamine (2.2 mL, 16.0 mmol), HATU (4.5 g, 12 mmol) and 2-methoxyl-N-methylaniline (1.19 g, 8.7 mmol). The mixture was stirred at rt for 16 hrs and water was added. The organic layer was separated, washed with NaHCO3, dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography eluting with 20% ethyl acetate in hexane to afford 5-bromo-4-chloro-2-hydroxy-N-(2- methoxy-phenyl)-N-methyl-benzamide (300 mg). MS [M+H]+: 371.9; tR = 2.60 min (method 1)Alternatively, a mixture of 5-bromo-4-chloro-2-hydroxybenzoic acid (5 g, 19.9 mmol), 2-methoxy-N-methyaniline (3.13g, 22.9 mmol) and P2O5 (5.36g, 37. 8 mmol) in anhydrous xylene was heated at 60 0C for 2 hrs and then refluxed for 17 hrs. The mixture was concentrated and purified via silica gel flash column chromatography eluted with ethyl acetate in hexane (20%) to give 5-bromo-4-chloro-2-hydroxy-N-(2- methoxy-phenyl)-N-methyl-benzamide (3.3 g).

The synthetic route of 2-Methoxy-N-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124610; (2008); A1;,
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